Rivaroxaban is a direct Factor Xa inhibitor with Ki and IC50 of 0.4 nM and 0.7 nM, respectively, in a cell-free assay. Rivaroxaban is highly selective against human factor Xa, more than 10 000 times more selective than against other biologically relevant serine proteases.

 

Brand: BCM

 

Target: Factor Xa; Thrombin

 

Signaling Pathways: Metabolism; Proteases/Proteasome

 

In Vitro: In rat and rabbit models of arteriovenous shunt, oral Rivaroxaban reduced arterial thrombosis (ED50:5.0 mg/kg and 0.6 mg/kg). Rivaroxaban dose-dependently reduced venous thrombosis in a rat model of venous stasis (ED50:0.1 mg/kg). Rivaroxaban plasma pharmacokinetics were linear over the study dose range of 0.3 to 3 mg/kg in dogs and 1 to 10 mg/kg in rats. The plasma clearance of Rivaroxaban was 0.3 L/(kg·h) in dogs and 0.4 L/(kg·h) in rats. The volume of distribution (V(ss)) was stable: 0.4 L/kg in dogs and 0.3 L/kg in rats. The oral elimination half-life of Rivaroxaban in both species was relatively short (0.9-2.3 h).

 

In Vivo: Rivaroxaban is an oral inhibitor of activated factor X directly (Ki: 0.4 nM) and also has an inhibitory effect on prothrombin activity (IC50:2.1 nM), which is used for the prevention and treatment of arteriovenous thrombosis. For purified human and rabbit FXa,Rivaroxaban had similar affinity (IC50:0.7 nM and 0.8 nM) but poor affinity for rat FXa (IC50:3.4 nM). In plasma, Rivaroxaban showed comparable inhibition of endogenous FXa in humans and rabbits (IC50:21 nM) but was less effective in rat plasma (IC50:290 nM). Rivaroxaban, a P-gp substrate with polarized transport properties and high permeability in Caco-2 cells, did not affect P-gp-mediated drug transport even up to 100 μM in vitro.

 

Melting Point: 228-229°C

 

Boiling Point: 732.6±60.0 °C(Predicted)

 

pKa: 13.36±0.46(Predicted)

 

Solubility: Soluble in DMSO. Insoluble in Water; Insoluble in Ethanol.

 

GHS: GHS09

 

Isomeric SMILES: C1COCC(=O)N1C2=CC=C(C=C2)N3C[C@@H](OC3=O)CNC(=O)C4=CC=C(S4)Cl  

 

InChIKey: KGFYHTZWPPHNLQ-AWEZNQCLSA-N  

 

InChI: InChI=1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1

 

Attribute
[Chem Name]	5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide
[Synonym]	Rivaroxaban; BAY 59-7939
[CAS No.]	366789-02-8
[EINECS]	685-132-2
[MDL No.]	MFCD11974010
[Formula]	C19H18ClN3O5S
[Molecular]	435.88
[Form]	Solid powder
[Storage]	Inert atmosphere, 2-8°C

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